


Another Lesson

by thewinchesterlifestyle



Series: John's Lessons [2]
Category: Supernatural
Genre: Age Difference, Barebacking, Blindfolds, Bondage, Bottom Castiel, Cheating, Cock Cages, Dehumanization, Dildos, Dirty Talk, Dubious Consent, Exhibitionism, Face-Fucking, Fingering, Forced Feminization, Gags, Humiliation, M/M, Name Calling, Objectification, Older John, Orgasm Denial, Restraints, Rough Sex, Sexual Grooming, Size Difference, Size Kink, Small Penis, Sounding, Spitroasting, Teen Castiel, Teen Dean, Threesome, Top Dean, Top John, Verbal Humiliation, Voyeurism, teaching sex
Language: English
Status: Completed
Published: 2017-06-22
Updated: 2017-06-22
Packaged: 2018-11-17 11:58:03
Rating: Not Rated
Warnings: Underage
Chapters: 1
Words: 3,088
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11274945
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: “You’re late.” Castiel blinked as he took in the sight of John Winchester standing there with an unimpressed look on his face. “I told you I’d give you boys another lesson. Now come here.”





	Another Lesson

**Author's Note:**

> Written for multiple prompts for a continuation. 
> 
> I tried to get a good balance of the various kinks/scenarios requested (I didn't know this was so popular) so I hope EVERYONE who wanted a continuation of "An Unexpected Lesson" likes this.
> 
> Tagged underage because states/countries age of consent vary.

Castiel pushed open the door to the Winchester’s and stepped inside, shutting and locking it behind him, as he kicked off his shoes. “Dean?” he glanced at his phone, the text message telling him to come by at six and to let himself inside. “Dean?”

“You’re late.” Castiel blinked as he took in the sight of John Winchester, naked and hard, standing there with an unimpressed look on his face. “I told you I’d give you boys another lesson. Now come here.”

His breathing caught and Castiel swallowed as he tried not to look at his boyfriend’s father. He could still remember the feeling of _that_ monstrous cock fucking his ass while Dean watched in muted shock. He could still remember enjoying it and he hadn’t been able to stop thinking about it.

“ _Now_.” The order snapped out and Castiel took a few shaky steps forward, still not looking, as a hand curled around him. “Come along.” He was systematically stripped, clothing discarded on the floor, before his attention was drawn to the items on the coffee table. “Your lessons start before Dean’s. I do want my son’s boyfriend to be experienced in giving pleasure so my son enjoys himself.”

Castiel shuddered when John picked up his cock and his body jerked when the older man started to rub against the tip.

“You’re going to want to relax. Sounding could hurt if you don’t calm yourself.” Castiel found himself held as John started to work a thin rod into his cock. It felt wrong and he whined, body shuddering and tense. “Be a good whore.” It was finally inserted, the round ball resting on top. “I knew I wouldn’t need a big one.”

Metal was wrapped around his cock and a lock snapped in place as Castiel’s breathing hitched.

“Such a tiny dick.” John touched his caged cock and moved down to fondle his hairless balls, “And matching tiny balls.”

Castiel’s face flushed and he looked away. Humiliation burned inside of him and he tried not to look at John’s cock, gigantic and thick, as John continued to touch and comment on his cock. He knew his cock was tiny but Castiel tried not to think about it when compared to others.

“Two inches? Right?” the voice was full of amusement, “At least you have an ass to make up for it. A sweet little _cunt_ for my boy to get off in.”

John moved away and Castiel sagged against the couch as he watched Dean’s father pick up a large ring with straps attached.

“Open up.” A warm hand curled around his jaw and Castiel hesitantly opened his mouth, humiliation bitter on his tongue from John’s comments, as the large ring was pushed into his mouth. It turned and the metal pushed against the roof of his mouth as the ring gag forced his mouth wide open. “There we go.” It was secured behind his head.

Next Castiel’s arms were tied behind his back with a tie and another tie wrapped around his head like a blindfold. He shivered as large hands touched his body, commenting on how small and soft he was, as Castiel whimpered.

“You’re going to practice cockwarming today until Dean comes home and then I’m going to begin my son’s second lesson.” Castiel found himself guided over the arm of the couch and large hands spread his cheeks to offer his hole to John’s gaze. “My boy hasn’t used this, has he?” a callused thumb rubbed against his hole and Castiel jerked, hole clenching, at the pressure. “Shame. He’s wasting a perfectly good cunt.”

Castiel’s cheeks flushed further.

“Are you going to be a good girl for me?” Castiel jerked at the comment and he tried to protest, he wasn’t a girl, but it was hard to talk with the large gag and Dean’s father didn’t seem to care about his reaction.

A wet, lube slick finger rubbed against his hole and then started to work inside. It burned and ached and Castiel whined brokenly into his gag, trembling and shaking, as John’s other hand fondled his balls.

His hole spread open to accept John’s thick finger pushing inside and crooking until it brushed his prostate. Immediately pleasure flared inside of him and Castiel moaned, body rocking slightly, as John rubbed against his prostate without pause.

Pleasure built and built and built inside of him as Castiel’s moans echoed in the living room, his body warm and tight, as he shoved back into John’s finger and tried to fuck himself on it. It felt _so good_ and he wanted to come, he wanted to come on the feeling of John’s finger.

Castiel’s mind was fuzzy with pleasure and his body warmed as John kept rubbing but Castiel couldn’t come. He shivered and whined, wordlessly begging for release, as a second finger was added. It ached, the denial, but the sound and cockcage kept him on edge.

Occasionally John’s fingers brushed his prostate sending more pleasure rushing through him but for the most part John focused on finger fucking him until a hum of approval sounded.

“There we go.” John’s voice was full of pleasure, “You were such a good girl for me. Letting me get that cunt all loose and slick for my dick.”

Strong hands wrapped around him, hauled him up and Castiel stumbled along as John guided him through the living room. He couldn’t see and his ass ached from where John had worked three fingers inside of him.

They stopped and he felt John move, hands briefly leaving him, until they were tugging him down. Castiel almost fell, body barely maintaining his balance, until he felt the thick and large head of John’s cock pushing against his hole.

Castiel’s heart stopped as John pulled him down so he sunk onto John’s monstrous cock, thick inch by thick inch spreading his aching hole wide, until his ass was resting on John’s lap and he was completely impaled on Dean’s father’s cock once more.

Somehow it felt bigger in this position and Castiel squirmed, whining lowly at the undeniable pain and ache in his ass, as John moaned in enjoyment and patted his thigh. “Good girl.” John praised, spreading Castiel’s legs wide so the insides of his legs were pressed against the outside of John’s and he was completely exposed to the room.

His ass clenched and John moaned lowly again.

“Your cunt feels so good warming my dick.” John’s hand stroked Castiel’s stomach, settling on his lower belly, as he was guided back and his bound arms were trapped between their bodies. “You’ll practice warming my dick while we wait for Dean. I don’t want to hear a sound from you, slut.”

Castiel was completely humiliated as he listened to John praising him for being a good _girl_ and telling him how good his _cunt_ felt, how he was born to house a cock in his tight little hole and how when John was finished with his lessons he’d be the perfect little bottom whore for Dean.

He wasn’t sure how long he sat there, John Winchester’s thick and long cock buried balls deep in his ass, before the front door opened and shut.

“Dad?” it was Sam’s voice and Castiel jerked, body tense. He didn’t know where he was or if Sam could see them. “Who is—”

“Your Dad has a friend over, Sam. Please go to your room and do your homework.”

Footsteps padded away, Sam not protesting or coming into the room, as Castiel whined into his gag as humiliation once more flared inside of him. It was almost a relief when the door opened again and this time it was Dean.

“Dad?” Dean’s voice sounded off and Castiel turned his head away from where he’d heard Dean’s voice. He was embarrassed by his position and the knowledge that he’d been moaning loudly for John’s fingers hours ago. “What are you doing?”

“I started Castiel’s lesson early.” The tone was reasonable. “He needed to learn how to be an obedient little cockwarmer.”

Dean released a choked sound, “Dad that isn’t—”

“What did I say to you about questioning me?”

Dean muttered something and Castiel closed his eyes as John’s hands started moving over his naked body again, reaching between his spread legs and rubbing against where his hole was spread taut around John’s cock.

“Now the important part of this lesson is that when you have such a pretty little thing to warm your dick you make sure to thoroughly prepare your whore for her job.” If Dean thought anything of the _her_ part of John’s comment he didn’t say anything. “Take a good look.”

He heard footsteps and knew that Dean was standing before them. Dean _always_ obeyed his father.

“Notice how I dealt with the useless little dick?” fingers touched his caged and plugged cock, “A good cockwarmer doesn’t need to come. They’re only there for _your_ pleasure. A warm cunt to nestle inside while you relax. You should keep her caged frequently and plugged when you use her cunt or mouth.”

Dean shifted and Castiel’s cheeks flushed as John’s hand moved up.

“Why did you…why is his mouth…?”

“Because a good whore is open at both ends for use at _any_ given moment unless you want to muffle her sounds then you use a ball-gag.” Castiel felt himself shifted up and jerked as he almost fell forward but a strong hand kept him in place so he was bent in half, John’s cock still lodged in his ass, while his face was directed forward. “Now the first lesson tonight is fucking your whore’s mouth.”

Castiel whined lowly when a finger rubbed once more against his taut hole. Pleasure twisted inside of him and he flushed darker. “But he’s—”

“I’m trying to teach you the best way to fuck her and you’re being ungrateful.” John’s fingers tightened where they were gripping him. “Now take your dick out and get it wet in her slutty little mouth.”

His face was still flushed with humiliation as the sound of a zipper and clothing rustling caught his attention.

“Good.” John’s voice was still rough with displeasure, “Now guide your dick into her mouth, I made sure the gag would keep her mouth open so she doesn’t bite.” Castiel couldn’t see but he felt Dean’s cock pushing through the ring of his gag and slowly filling his mouth. “Grip her head and start fucking that hole like it’s a wet cunt you need to get off in.”

John’s hand on his back kept him in place and Dean’s hands gripped his face as his boyfriend started to hesitantly fuck his face. Castiel choked and gagged when Dean’s cock pressed in deeper. He felt Dean’s fingers tense and his boyfriend paused a sound of concern escaping.

“Keep going.” John’s voice snapped out, “Your girl is never going to learn how to be a good set of holes if you keep hesitating.”

Dean’s fingers clenched again but he started thrusting quicker and Castiel gagged several times, struggling to breathe when Dean’s cock choked him, until he managed to relax his throat.

“See…your whore is _learning_. She learned to relax her throat after choking on your dick and it’s a lesson you’ll thank me for when she takes your dick down her throat like a pro.”

Castiel’s fingers clenched where they were bound behind his back and his ass tightened around John’s cock when Dean choked him again as he fucked forward. He could hear how Dean’s breathing was hitching and he could feel the way Dean’s pace started to fall off as his fingers dug into his face to keep him in place.

“Really give it to her.” John goaded as Castiel squirmed on his cock and focused on keeping his throat relaxed. “She really likes that. You should feel how your whore is tightening down on me.”

Dean was pounding down his throat now and Castiel gagged, body tensing and seizing, before Dean was thrusting forward and his hips jerked as he emptied his release down Castiel’s throat. He gagged and choked, throat working to swallow, as Dean moaned in pleasure.

“See how good that was? You got better as you let go of your control. That is one of your problems. You need to see her as a warm body to give you pleasure. She’s meant to be a warm set of holes for _your_ use and _your_ pleasure.”

Castiel was guided back up so he was sitting on John’s cock once Dean’s softening cock slipped free. “But Cas is my boyfr—”

John cut him off, “See this?” John’s hand curled around his small caged cock, “See how useless this is? _This_ is a whore and this body was designed to facilitate seeking pleasure for whoever is using it. This cunt,” fingers rubbed against his rim again, “And this mouth,” a hand touched his held open mouth, “Are nothing more than holes for dicks to get off in. Your dick and someone else’s dick if you decide to share her with someone else. This,” hands gripped him, "is a warm body to  _use_ and get off in. Don't waste time using meaningless labels."

He was hauled up, John’s cock slipping from his loose hole and bent over what felt like the arm of a chair. Castiel jerked when he felt fingers tugging on his rim and then lube being added.

“You want to make sure the cunt you’re using is slick and sloppy unless you want a tighter, rougher fuck. In one of your next lessons I'll have you fuck her cunt dry with a little lube on your dick so you can know the difference.” Castiel tried not to think about how that would feel. His ass burned after prep so he couldn't imagine a  _dry_ fuck.

John’s thick cock pushed into him from behind once more, fingers knotted in his hair to yank harshly and another hand gripped his hip as John started to roughly pound into him from behind. Castiel whined and moaned each time the older man’s cock nailed his prostate causing him to clench and shudder.

Castiel could only lie there, moaning and gasping, as John brutally pounded into him from behind. He could feel pleasure building inside of him, just like last time, as John’s pace picked up and the loud, ringing smack of John thrusting balls deep into him on each snap of his hips filled the room along with grunts of pleasure. His body was tight with unwanted and unexpected pleasure as John roughly used him with the goal of only achieving his own pleasure.

He could hear Dean off to the side, shifting and not reacting, as John continued to pound into him. “See how good she is at taking it? How hungry she is for a big dick in her sweet little cunt? You need to make sure to use at least one of her holes every single day so she knows her place is purely giving you pleasure. That's all she exists for. But until you're ready I'll make sure to help you in breaking her in until she learns her place.”

John’s pace picked up until he was slamming balls deep into Castiel’s hole each time and Castiel could only lay there, bent over and moaning as several thrusts nailed his prostate. Pleasure curled inside of him and was rapidly followed by shame when John’s rough treatment and comments continued to have him squirming in arousal.

The rough manhandling and being referred to as a girl shouldn’t be having this effect on him. An effect that was coming out of left field the longer he was used in front of his boyfriend by his boyfriend’s father.

“See? See how much the little whore likes it? See how she’s moaning like a slut?” John’s fingers dug in and then he was slamming deep, groaning in appreciation, as his hips jerked and Castiel knew John had come in his ass without a single care. "She  _needs_ her holes used and fucked full."

He whined when the softening cock slipped from his wrecked hole and come leaked out. Castiel clenched and shifted, on edge and wanting desperately to come, as John kept a hand braced on him.

“As soon as you’re hard again I want you to show me what you learned, Dean.” John spoke and Castiel shivered as he remained bent over with his ass offered for their view. “I want you to fuck her cunt and I want to hear her moaning like a bitch in heat by the time you’re finished.”

“But—”

“No, Dean. I’m trying to show you the proper way to fuck and all of the enjoyment you can get from sex. I saw the horrible, fumbling job you were doing last time.” John’s hand kept him in place as his release leaked out of Castiel’s gaping hole. “Now pick up that toy over there…yes that one and the large ball-gag. No. The _bigger_ ball-gag. The one that'll keep her mouth stretched wide open. Bring them here.”

Castiel’s breathing hitched.

“Remove the gag she has and replace it with that one.”

Shaking fingers removed the large ring gag in his mouth and Castiel whined lowly as he closed his mouth. His tongue darted out to wet his lips. His jaw  _ached_ and he clenched his teeth against the pain.

“Open up.” Castiel slowly opened his mouth knowing what was expected of him at this point and Dean pressed the large ball into his mouth. This time it filled his mouth and kept it held open wider. He released another low whine at the ache in his jaw. It _hurt_. “Secure it.”

Dean followed his father’s instructions as Castiel remained bent over and completely exposed.

“Good. Now I want you to use this toy and fuck her cunt with it until you’re ready.” Castiel tensed, not remembering the size of the toy, as Dean moved and paused. “Her cunt needs to get used to taking large objects. Once you get further on in your lessons I’ll teach you about object insertion and hole gaping.”

The large, thick head of the toy pushed against his sore hole and started to sink in as Castiel whimpered into his gag. Dean paused and the toy didn’t go any further until John released an impatient sound. He wasn't near prepared enough for a toy that thick.

“Give it here and I’ll show you how to do this too.”

**Author's Note:**

> There you have it. That was my attempt to give the overwhelming number of requests for a continuation and to try to get the majority of the kinks blended together.
> 
>  
> 
> Please leave a comment and let me know what you thought. Remember comments are motivation for continuing to write and post fanfics!


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